Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-12-19
2000-01-18
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5482662, 5482666, A61K 3141, C07D40310
Patent
active
060158255
DESCRIPTION:
BRIEF SUMMARY
This invention relates to triazoe derivatives which have antifungal activity and are useful in the treatment of fungal infections in animals, including humans.
Thus the invention provides compounds of the formula: ##STR2## and their pharmaceutically acceptable salts, where Ar is a phenyl group substituted by 1 to 3 substituents each independently selected from halo and CF.sub.3 ; ##STR3## wherein Z is H or F, and in which Het is a 5-membered nitrogen-containing aromatic heterocyclic group optionally containing an oxygen or sulfur atom and attached to the phenyl, pyridyl or pyrimidinyl group by a carbon or nitrogen atom and optionally substituted by 1 to 3 substituents each independently selected from halo; C.sub.1 -C.sub.4 alkyl; (C.sub.1 -C.sub.4 alkoxy)methyl; 2-(C.sub.1 -C.sub.4 alkoxy)ethoxymethyl; 2-hydroxyethoxymethyl; cyanomethyl; --NR.sup.1 R.sup.2 or --CH.sub.2 CONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are each independently H or C.sub.1 -C.sub.4 alkyl; phenylthio or phenyl-(C.sub.1 or C.sub.2 alkyl) in both of which said phenyl group is optionally substituted by halo, trifluoromethyl or C.sub.1 -C.sub.4 alkyl; --NHCO(C.sub.1 -C.sub.4 alkyl); --NHSO.sub.2 (C.sub.1 -C.sub.4 alkyl); --NHCONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are as defined above; mercapto; and --S(O).sub.n (C.sub.1 -C.sub.4 alkyl) where n is 0, 1 or 2.
"Halo" means F, Cl, Br or l. Preferred alkyl groups are methyl, ethyl and isopropyl, and preferred alkoxy groups are methoxy and ethoxy.
Z is preferably H.
Preferably, "Het" is a pyrazolyl, imidazolyl, triazolyl, thiadiazolyl, oxadiazolyl, pyrrolyl, thiazolyl or tetrazolyl group, optionally substituted as defined above, particularly a pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, pyrrol-1-yl, thiazol-5-yl or tetrazol-5-yl group, these groups being optionally substituted by 1 to 3 substituents as defined above, and particularly by 1 to 3 (preferably by 1 or 2) substituents each independently selected from chloro, bromo, fluoro, iodo, C.sub.1 -C.sub.3 alkyl, amino, ethoxymethyl, 2-methoxyethoxymethyl, 2-hydroxyethoxymethyl, methylthio, methanesulphonyl, mercapto, phenylthio, methanesulfonamido, 3-methylureido, cyanomethyl, carbamoylmethyl, acetamido and benzyl.
The most preferred compounds are either unsubstituted or have one substituent as defined above.
Specific examples of "Het" include pyrazol-1-yl, 3-aminopyrazol-1-yl, 1-ethoxymethylpyrazol-4-yl, 1-ethoxymethylpyrazol-5-yl, 4-bromo-pyrazol-3-yl, 3-methanesulfonamidopyrazol-1-yl, 3-(3-methylureido) pyrazol-1-yl, 3-acetamidopyrazol-1-yl, 1-methylpyrazol-5-yl, 1-methylpyrazol-3-yl, 1-ethylpyrazol-5-yl, 1-isopropylpyrazol-5-yl, 1-ethoxymethylpyrazol-5-yl, 1-carbamoylmethylpyrazol-3-yl, 1-cyano-methylpyrazol-3-yl, pyrazol-3-yl, pyrazol-4-yl, 3-methylpyrazol-4-yl, 1-methylimidazol-2-yl, imidazol-1-yl, 2-methylimidazol-1-yl, 1-ethoxymethyl-2-phenylthioimidazol-5-yl, 1-ethoxymethylimidazol-2-yl, 4-methylimidazol-1-yl, 1-ethoxymethylimidazol-5-yl, imidazol-2-yl, 1-methylimidazol-5-yl, 1-ethylimidazol-5-yl, 1-methyl-2-phenylthioimidazol-5-yl, imidazol -4-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1-ethoxymethyl-1,2,4-triazol-5-yl, 1-ethoxymethyl-3-methylthio-1,2,4-triazol-5-yl, 1,2,3-triazol-4-yl, 1-(2-methoxyethoxymethyl)-1,2,3-triazol-5-yl, 1-benzyl-1,2,3-triazol-5-yl, 1-(2-hydroxyethoxymethyl)-1,2,3-triazol-5-yl, 5-methyl1,2,3-triazol-4-yl, 3-methylthio-1,2,4-triazol-1-yl, 1-ethoxymethyl-1,2,3-triazol-5-yl, 4-methyl-1,2,4-triazol-3-yl, 3-mercapto-4-methyl-1,2,4-triazol-5-yl, 1-methyl-1,2,4-triazol-5-yl, 1-ethoxymethyl-1,2,3-triazol-4-yl, 2-ethoxymethyl-1,2,3-triazol-4-yl, 1,2,4-triazol-4-yl, 4-chloro-1,2,3-triazol-5-yl, 4-bromo-1,2,3-triazol-5-yl, 4-iodo-1,2,3-triazol-5-yl, 4-fluoro-1,2,3-triazol-5-yl, 1,2,4-triazol-3-yl, 5-methanesulfonyl-1,2,4-triazol-3-yl, 3-methanesulphonyl-1,2,4-t
REFERENCES:
patent: 5629332 (1997-05-01), Kodama et al.
patent: 5648372 (1997-07-01), Naito et al.
Cram and Hammond, "Organic Chemistry", McGraw-Hill Book Co., NY (1964) 2nd ed., pp. 565-567.
Bell Andrew Simon
Fray Michael Jonathan
Marchington Alan Patrick
Richardson Kenneth
Stephenson Peter Thomas
Ginsburg Paul H.
Morris Patricia L.
Pfizer Inc.
Richardson Peter C.
Zielinski Bryan C.
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